NOT Your Grandma's Book of Progressive Erotica: Vol 2

Full Workout

It had been over five years since my best friend and I had parted ways after highschool. I went to a college up north and he went to a university in Ottawa. Since then, we hadn't spoken, even though I tried my best to stay in touch with him. We had been through so much over the years and to have it end like that – with a wave of a hand, or in the blink of an eye – was the crown on what was a crumbling friendship on the inside.

Remembering that his mom was always coming home in her work attire when I went over to play video games, I thought I should track her down for some fitness advice. I had just graduated and was starting my new job at a local mechanic's shop. Throughout my college years, I had put on several unneeded pounds of fat due to a poor diet and lack of a girlfriend. Turning around my life was possible, but I needed a personal trainer.

Sure enough, searching for what I remembered from my teenage years, I found her business online. She seemed to be doing rather well and had steady classes throughout the week. There was a free fitness assessment like most places to get you to try it out and I figured I would give her a call. At first, she didn't know who I was, but then it all came back as I began to recall study nights and video game sleepovers. She said there was an opening the next day at four in the afternoon and since I wasn't working full-time yet, I agreed to come by at that time.

When I got there, I realized what a personal trainer truly was. It wasn't awkward and it most certainly wasn't easy. I told her my goals, lifted my shirt to show my flabby stomach and then she got me to do basic movements and exercises to gauge where I was at. After the free assessment, I could tell she was not going to take it easy on me. I was drenched in sweat and there she was, five foot nothing, long black hair in a ponytail and toned to perfection. I envied her sculpted body, but it was only a matter of time before that envy went away.

Fast forward to three months later, twenty pounds lighter and a shirt size smaller; I even needed to buy new pants due to the weight I was shedding. She had done it – I had done it – she had finally whipped me into the best shape of my life. Girls were beginning to notice me more and my job had become a lot easier as well. I couldn't thank her enough for the results I was seeing.

The day of my usual appointment for a check-in, she informed me that I could do everything on my own at a gym and it would cost me less as well. I felt a bit letdown, like a girl breaking up with me. I was used to the routine and being told what to do that I wasn't sure my inner voice would be enough motivation to stay on track. She told me she had faith in me and then began our routine.

At the end of it, I felt like I still had some energy left and she said I could always burn it off with a run later on. As I took off my sweat drenched t-shirt and put on a clean one for the drive home, she commented on how good looking I now was. I laughed and thanked her. I told her it was all because of her that I was looking so good.

"You should get tips when someone reaches a milestone like this," I told her as I pulled my shirt over my head. It stuck a bit on my shoulders and she came over to help me so I didn't struggle as she laughed. Her smiling face turned serious as she stood in front of me and then ran her fingers along my six pack.

"I'll take that tip right now if you're offering." I stared down into her brown eyes and felt the excess energy of mine concentrate in my crotch area – let's be honest here, it was blood flowing to my dick to form an erection. I nodded and she quickly ran around the workout room, locking doors and closing blinds, returning to where I was standing with a workout mat. As she laid it down in front of me, I felt my dick pitching a vertical tent through my track pants.

Turning around, she jumped at me, wrapping her legs around my waist and I grabbed her firm ass to hold her up. She put her hands on my chin with it's five o'clock shadow and began to make out with me like we were both in highschool detention. After a few minutes of kissing and my dick becoming fully erect, I set her down and she pulled my dick out; revealing my red boxer briefs and a dick, anxiously sticking its head out the side of them. She bent over slightly and put her mouth on it instantly as she pulled it out. She was too short for me to reach her ass, so after a few minutes of her sucking me off, she took off her runners and dropped her yoga pants like the world was going to end –sans panties I might add.

She spit into her hand and then rubbed her pussy. Without a moment's notice, she then jumped at me again and I caught her with my hands on her firm ass once more. We re-positioned so that I could slide my dick into her and then I drilled her pussy while in the standing position. I hadn't fucked a girl in this position before, but then, I never had the strength to do it before. She moaned as my thick dick pounded her. I might not have had the length, but I most certainly had the girth.

Setting her down, she walked to the mat she had brought over earlier and let me fuck her on her back with her legs up in the air in a 'v' shape. For a woman who was in her late forties at least, she was in great shape. Her face showed wrinkles from laughing and smiling a bit too much, as well as the cigarettes I remembered her smoking back when I was in highschool.

After pounding her for an extended period of time, I was beginning to get winded. I pulled out, noticing how wet she had made my dick and switched positions with her. Allowing her to ride on top of me was fucking great. If you ever get the chance to fuck a milf, do yourself a favour and don't second-guess it. She fucked me better than any girl had throughout highschool and college. If I could, I'd keep fucking her, but if her husband was to find out, I'd be a dead man; she hadn't mentioned her husband at all, so I wasn't entirely sure if I was in the clear.

Riding me like the experienced woman she was, she clawed at my chest as we both came at the same time. She squirted all over my dick and balls, and the workout mat as well. I groaned as I came inside her pussy and she moaned back as she relaxed with my dick still well inside her. Holding still in our puddle of sin, we both caught our breaths until she spoke.

"You know, maybe you should still come see me once a month. After all, I'm beginning to like this idea of being tipped."